DETAILED ACTION
This Office Action is in response to Applicant’s Amendment and Remarks filed on 24 February 2026 in which claims 1 and 10 were amended to change the scope and breadth of the claims.
Claims 1-16, 18 and 20-23 are pending in the current application. Claims 1-10, 13-16, 18, 22 and 23 are withdrawn as being drawn to a non-elected invention. Claims 11, 12, 20 and 21 are examined on the merits herein.
Claim Status
Some of the claims submitted 24 February 2026, previously indicated as withdrawn, do not contain the correct status identifier (e.g. withdrawn).
Election/Restrictions
Previously presented claims 2-4, 6-10 and 14-16 remain withdrawn as being drawn to a non-elected invention.
Claims 1, 5, 13, 18, 22 and 23 are now withdrawn as being drawn to a non-elected invention, because independent claim 1 has been amended to require a crosslinked product “wherein the alkyl polyglucoside is cross-linked via hydroxypropyl linkages formed by reaction with epichlorohydrin and/or Cl-CH2CH(OH)-CH2-Cl”.
Applicant's election with traverse of Group I in the reply filed on 28 July 2025 is acknowledged.
The restriction was made final in the Office Action mailed 21 August 2025. As noted in the Office Action mailed 21 August 2025:
The compound of Group I contains one glucoside, and one citrate modified at one carboxylic
group.
The compound of Group II, contains two glucosides linked via a citrate modified at two carboxylic
groups.
The compound of Group IIII, contains two glucosides linked via a -CH2-O-CH2- moiety, and
modified at only one position with a citrate modified at one carboxylic group.
The compound of Group IV, contains two glucosides linked via a -CH2-O-CH2- moiety, and a citrate
modified at two carboxylic groups.
To summarize, Groups II-IV are directed to crosslinked glucosides, Group I, which was elected for examination is not drawn to a crosslinked glucoside.
As a result of the election, claims 2-4, 6-10 and 14-16 were withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected invention.
In view of the amendment to require claim 1 to be crosslinked, claims 1, 5, 13, 18, 22 and 23 are also withdrawn as being drawn to a non-elected invention.
Withdrawn Rejections
Applicant’s amendment, filed 24 February 2026, with respect to the rejection of claims 1, 5, 11-13, 18 and 20-23 under 35 U.S.C. § 112(b), second paragraph, for indefiniteness, has been fully considered and is persuasive.
The rejection is hereby withdrawn.
Modified Rejections
The following are new ground(s) or modified rejections necessitated by Applicant's amendment, filed on 24 February 2026, where the limitations in pending claims 1 and 10 as amended now have been changed. Therefore, rejections from the previous Office Action, dated 21 August 2025, have been modified and are listed below.
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claim(s) 11, 12, 20 and 21 (all in-part) are rejected under 35 U.S.C. 103 as being unpatentable over Jin et al. (J. Surfact. Deterg., 2016, vol. 19, pp. 885-891, cited in previous Office Action) in view of O’Lenick, Jr. et al. (US Patent No. 7,087,571; hereinafter the ‘571 Patent, cited in previous Office Action) and O’Lenick, Jr. et al. (US Patent No. 8,268,766; hereinafter the ‘766 Patent, cited in previous Office Action).
Jin et al. is concerned with the synthesis of alkyl monoglucoside citric monoester (title). The alkyl groups vary in length where R is a C8, C10 or C12 alkyl, and the reaction is performed in the presence of a strong base:
PNG
media_image1.png
168
448
media_image1.png
Greyscale
(scheme 1; the difference between the structure is pointed out with an arrow, i.e. “-CH2-CH(OH)-CH2-”). Disodium alkyl polyglucosides citrate (APG-EC) prepared from corn starch, citrus juice and natural oil, is a sugar-based green anionic surfactant that is safe and mild (p.885, first para). Furthermore, APG-EC has reduced irritation to eyes and skin. The citrate functionality improves the solubility issues with APG. “Because of its excellent water-solubility, APG-EC aqueous solutions remain clear and bright after prolonged storage near 100 °C.” (p.885, first para). It also has many improved performance attributes, including excellent foaming, and hard water resistance. It can be applied to cosmetics, beauty care products and detergents. Jin et al. teach other alkyl polyglucosides (APG) derivatives have been prepared, including sulfonate and sulfosuccinate APG (p.885, first para).
Jin et al. do not expressly disclose a polymerizing agent as recited in claims 11 and 12, or a structure incorporating the polymerizing agent of claims 11 and 12, i.e. “-CH2-CH(OH)-CH2-”.
The ‘571 Patent teaches a composition having an alkyl polyglucoside of formula (a),
PNG
media_image2.png
100
188
media_image2.png
Greyscale
, where R is an alkyl having 8 to 22 carbon atoms; R1, R2, R3 and R4 are independently selected from the group consisting of -CH2CH(OH)CH2-R12 and H, with the proviso that R1, R2, R3 and R4 are not all H; R12 is
PNG
media_image3.png
58
240
media_image3.png
Greyscale
, a dicarboxylate group, where M is selected from Na, K, and NH4 (claim 1). The above compound is prepared by reacting glyceryl chlorohydrin (Cl-CH2-CH(OH)CH2OH) with maleic anhydride (a dicarboxylate containing moiety). The reaction conditions are mild, and employ sodium methylate (col.11, examples, lines 20-67). The obtained surfactants have “outstanding detergency and foam properties as well as emolliency properties and humectant properties. These surfactants are of particular importance for use in personal care applications like bubble bath, shampoos and body wash. They are also very good additives for hard surface cleaners and detergent systems” (col.11:62-67).
The ’766 Patent teaches preparing alkyl polyglucosides derivatized with sorbitan esters (title). The alkyl polyglucoside is reacted with Cl-CH2CH(OH)CH2-Cl and sorbitan ester:
PNG
media_image4.png
74
220
media_image4.png
Greyscale
(col.3-4). The ‘766 Patent teaches reacting alkyl polyglucoside with the sorbitan ester and a family of epoxy compounds allows for an excellent emulsifier to be obtained under mild aqueous conditions (col.3:57-63). The alkyl polyglucoside (examples 1-9), the sorbitan ester (examples 10-16) are mixed with 1,3-dichloroisopropanol and sodium methylate (examples 27-37). The 1,3-dichloro-isopropanol reacts with the first hydroxyl group to give the following intermediate:
PNG
media_image5.png
104
290
media_image5.png
Greyscale
(col.5: 9-15).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to incorporate an isopropanol linker between the glucoside and citrate of the disodium alkyl polyglucosides citrate taught by Jin et al.
The skilled artisan would have been motivated to react an alkyl glucoside with 1,3-dichloro-isopropanol prior to further functionalizing the alkyl glucoside with citric acid, because the ‘766 Patent teaches the reaction conditions are mild compared to the use of the strong sodium hydroxide base utilized in Jin et al.
The ordinary artisan would have been motivated to use the isopropanol linker -CH2-CH(OH)-CH2- because in the same field of endeavor for preparing surfactants, the ‘571 Patent and ‘766 Patent teach modifying alkyl polyglycosides with the isopropanol linker, which can subsequently be functionalized with a carboxylic acid containing moiety. The ‘571 Patent teaches an alkyl polyglucoside having an isopropanol linker conjugated to a succinate group, a disodium dicarboxylate group. The ‘766 Patent teaches an alkyl polyglucoside having an isopropanol linker conjugated to a sorbitan ester, a carboxylate group. Jin et al. teach an alkyl polyglucoside conjugated to a citrate ester, a trisodium tricarboxylate group.
The ordinary artisan would have been motivated to optimize the alkyl monoglucoside citric monoester of Jin et al., because Jin et al. teach alkyl polyglucoside functionalized with citric acid esters produce no irritation to the eyes, and have excellent storage stability. The compound also possesses other similar desirable properties described by the ‘571 and ‘766 Patent, including foaming, hard water resistance and water-solubility. Like the alkyl polyglucosides of the ‘571 and ‘766 Patents, it can be used in cosmetics, beauty care products and detergents in general.
Claims 11 and 12 are product-by-process claims. The ‘571 Patent teaches reacting the chloro glycerin with the maleic anhydride prior to functionalizing the alkyl polyglucoside. Thus, the product-by-process limitation of claim 11, wherein the isopropanol linker is first reacted with a carboxylate ester, was known before the effective filing date of the claimed invention. Thus, it would have been obvious to react the isopropanol linker with citric acid prior to functionalizing the alkyl polyglucoside.
The use of Cl-CH2-CH(OH)-CH2-Cl as a polymerizing agent was known, and taught by the ‘766 Patent. Thus, it would have been obvious to prepare the alkyl polyglucoside using Cl-CH2-CH(OH)-CH2-Cl, or 1,3-dichloro-isopropanol as recited in claim 12.
Thus, the claimed invention as a whole is prima facie obvious over the combined teaching of the prior art.
Response to Arguments
Applicant's arguments filed 24 February 2026 have been fully considered but they are not persuasive.
With respect to claims 11 and 12, Applicant acknowledges patentability is based on whether the resulting composition is shown in the art. Applicant argues there is no evidence the cited prior art would result in the same composition as that recited in the present product-by-process claims.
The above arguments have been carefully considered, but are not found persuasive. The present claims require (based on the product-by-process language, and examples in the Specification) an alkyl polyglucoside to be covalently modified with a functionalizing agent, i.e. 2-hydroxypropyl that is covalently bonded to citrate. While Applicant does not identify the 2-hydroxypropyl as a “linker”, it is not naturally present in citric acid. Additionally, the “2-hydroxypropyl” is a functional group that covalently links the alkyl polyglucoside to citric acid.
The prior art rejection explains why it would have been obvious to modify Jin et al., directed to an alkyl polyglucoside directly attached to citrate, with a 2-hydroxypropyl group, to arrive at the same structure presently claimed.
According to Example 1 of the present Specification, the product obtained from reacting the reagents recited in claims 11 and 12 has the following structure:
PNG
media_image6.png
146
332
media_image6.png
Greyscale
(referred to as Structure 1, p.16).
Page 19 of the Specification describes reacting epichlorohydrin with citric acid in the presence of NaOH in accordance with the teaching of He et al. (Journal of Colloid and Interface Science, 454, 2015, pp. 216-225) to give the following intermediate/reactant (i.e. functionalizing agent):
PNG
media_image7.png
142
204
media_image7.png
Greyscale
. This is then reacted in the presence of NaOH, with an alkyl glucoside to give Structure 1, above.
The limitation of claim 12 is drawn towards preparing the 3-chloro-2-hydroxypropyl citrate intermediate/reactant (functionalizing agent):
PNG
media_image8.png
143
204
media_image8.png
Greyscale
.
Structure 1 as drawn in the Specification appears to be missing a -CH2- group, which should be located at the position indicated by the arrow above (between the “-CH(OH)-” and “-O-”):
PNG
media_image9.png
146
332
media_image9.png
Greyscale
. Also see the abstract of He et al., which shows the following structures obtained from reacting starch (a polyglucose) with 3-chloro-2-hydroxypropyl citrate in the presence of NaOH:
PNG
media_image10.png
304
586
media_image10.png
Greyscale
According to He et al., the final structure should contain a polyglucose attached directly to the 2-hydroxypropyl group, which is attached directly to citric acid. Note there is a -CH2- between “-CH(OH)” and citric acid.
The ‘571 Patent and ‘766 Patent describe two different ways of obtaining an alkyl polyglucoside attached directly to 2-hydroxypropyl, which is attached directly to a carboxylic acid group.
The obviousness rational has been addressed above.
Making the modification of Jin et al., as taught by the ‘571 and ‘766 Patent would have resulted in a composition that is the same as the present claims. The methods described in the ‘571 and ‘766 Patents provide a reasonable expectation of success in preparing an alkyl polyglucoside modified with a 2-hydroxypropyl, which is attached to a citric acid, because they are also drawn towards an alkyl polyglucoside modified with a 2-hydroxypropyl group, which reacts at the carboxylate functional group/
In addition to the reasons above, the ordinary artisan would have had a reasonable expectation of success, because He et al. (as disclosed in the examples of the present Application) was able to prepare a polyglucose attached to the same functionalizing agent presently claimed (i.e. 2-hydroxypropyl covalently bonded to citrate).
The rejection is hereby maintained.
Conclusion
In view of the rejections to the pending claims set forth above, no claim is allowed.
THIS ACTION IS MADE FINAL. Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to BAHAR A CRAIGO whose telephone number is (571)270-1326. The examiner can normally be reached M-F: Noon-8pm ET.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Fereydoun Sajjadi can be reached at 571-272-3311. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/BAHAR CRAIGO/
Primary Examiner
Art Unit 1699
Prosecution Insights